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Cu-Catalyzed asymmetric Friedel–Crafts propargylic alkylation of phenol derivatives

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Abstract

A copper-catalyzed asymmetric Friedel–Crafts propargylic alkylation of electron-rich phenol derivatives with a variety of propargylic esters has been described. With Cu(OTf)2 decorated with a chiral tridentate ketimine P,N,N-ligand as the catalyst, asymmetric Friedel–Crafts propargylic alkylation of 3,5-dialkoxyphenol derivatives proceeded smoothly in high yields and with good to excellent enantioselectivities. The present study suggested that the presence of an electron-rich substituent on the meta-position of phenol is essential for the promotion of Friedel–Crafts propargylic alkylation, and the substrate bearing two electron-rich groups on both the 3,5-positions of phenol tends to give a satisfactory performance.

Graphical abstract: Cu-Catalyzed asymmetric Friedel–Crafts propargylic alkylation of phenol derivatives

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Publication details

The article was received on 26 Aug 2017, accepted on 05 Nov 2017 and first published on 06 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02133J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Cu-Catalyzed asymmetric Friedel–Crafts propargylic alkylation of phenol derivatives

    L. Shao and X. Hu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02133J

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